Tag: 441.34

Synthesis of novel chiral phosphine-olefin complexes and their evaluation as ligands in the rhodium-catalyzed asymmetric 1,4-addition was written by Stemmler, Rene T.;Bolm, Carsten. And the article was included in Synlett in 2007.COA of Formula: C26H28FeNP This article mentions the following:

Novel chiral phosphine-olefin complexes containing ferrocene and cyrhetrene backbones were synthesized and evaluated as ligands in the Rh-catalyzed 1,4-addition of phenylboronic acid to cyclohexenone. The highest efficiency in this series was observed with planar-chiral ligands (S_p)-1-(diphenylphosphino)-2-vinylferrocene and (S_p)-tricarbonyl[η⁵-1-(diphenylphosphino)-2-ethenylcyclopentadienyl]rhenium, which furnished the corresponding product with up to 71% ee. In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2COA of Formula: C26H28FeNP).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. Phosphine-catalyzed asymmetric reactions are now powerful and versatile tools for the construction of C–C, C–N, C–O, and C–S bonds and for the syntheses of functionalized carbocycles and heterocycles. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.COA of Formula: C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric synthesis catalyzed by chiral ferrocenylphosphine-transition metal complexes. I. Preparation of chiral ferrocenylphosphines was written by Hayashi, Tamio;Mise, Takaya;Fukushima, Motoo;Kagotani, Masahiro;Nagashima, Nobuo;Hamada, Yuji;Matsumoto, Akira;Kawakami, Sota;Konishi, Mitsuo. And the article was included in Bulletin of the Chemical Society of Japan in 1980.Computed Properties of C26H28FeNP This article mentions the following:

As chiral ligands for transition metal complex catalyzed asym. reactions, various kinds of chiral ferrocenylphosphines, which have planar chirality due to 1,2-unsym. substituted ferrocene structure and also have a functional group on the side chain of the ferrocene nucleus, were prepared (S)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine, (S)-N,N-dimethyl-1-[(R)-1′,2-bis(diphenylphosphino)ferrocenyl]ethylamine and their dimethylphosphino derivatives were prepared by lithiation of optically resolved N,N-dimethyl-1-ferrocenylethylamine. The 1-(dimethylamino)ethyl group on the ferrocenylphosphines was converted stereospecifically by nucleophilic substitution reactions into 1-methoxy-, 1-hydroxy-, 1-diphenylphosphino-, and several 1-(dialkylamino)ethyl groups. 1-(Diphenylphosphino)-2-(dimethylaminomethyl)ferrocene was optically resolved via its phosphine sulfide dibenzoyltartaric acid salt. The relationship between CD spectra of the chiral ferrocenylphosphines and the configuration of their chirality is discussed. In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2Computed Properties of C26H28FeNP).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. The synthesis of novel trialkylphosphines can be quite difficult, thereby limiting the scope of their chiral variants. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Computed Properties of C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Efficient P,N,N-type ligands for Ru(II)-catalyzed asymmetric cyclopropanations was written by Dai, Huicong;Hu, Xiangping;Chen, Huilin;Bai, Changmin;Zheng, Zhuo. And the article was included in Journal of Molecular Catalysis A: Chemical in 2004.Formula: C26H28FeNP This article mentions the following:

Novel chiral P,N,N-type ligands I (R = Me, R¹ = H, Me; R = Et, Ph, R¹ = H) derived from (R)-(S)-PPFNH₂-R and 2-pyridinecarboxaldehydes were employed in Ru(II)-catalyzed asym. cyclopropanation of styrene with Et diazoacetate. Up to 99% yield with 95% e.e. for cis-isomer and 90% e.e. for trans-isomer was obtained on Ru(II)/I (R = Me, R¹ = H). In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2Formula: C26H28FeNP).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Asymmetric catalytic performance is determined not only by the metal center but also by the chiral ligand selected.Formula: C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric cross-coupling reactions: enantioselective synthesis of alkenyl sulfides was written by Cardellicchio, Cosimo;Fiandanese, Vito;Naso, Francesco. And the article was included in Gazzetta Chimica Italiana in 1991.COA of Formula: C26H28FeNP This article mentions the following:

An enantioselective synthesis of alkenyl sulfides by cross-coupling reactions between (E)- or (Z)-ArSCH:CHBr (I; Ar = Ph, 2-naphthyl, 2-pyridyl) and Grignard or organozinc reagents, using chiral complexes as catalysts, is described. The process is sensitive to several factors, e.g., the nature of the substrate, the organometallic reagent, the ligand, and the metal complex used as catalyst. Optical purities of up to 57% were achieved. The resulting unsaturated thioethers have been transformed into optically active 1-alkyl-2-phenylethenes or MeCHPhCO₂H. A new method for the synthesis of the starting (Z)-I is also reported. In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2COA of Formula: C26H28FeNP).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. During the past two decades, tertiary phosphine catalysts have been applied extensively in a wide range of carbon–carbon and carbon–heteroatom bond-forming transformations. Chiral ligands coordinate to metal centers to create an asymmetric environment around the reaction centers, which eventually affects enantioselectivity and reaction rate.COA of Formula: C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis

Asymmetric Catalytic Hydrogenolysis of Aryl-Halide Bonds in Fused Arene Chromium and Ruthenium Complexes was written by Mercier, Audrey;Urbaneja, Xavier;Yeo, Wee Chuan;Chaudhuri, Piyali Datta;Cumming, Graham R.;House, David;Bernardinelli, Gerald;Kuendig, E. Peter. And the article was included in Chemistry – A European Journal in 2010.Formula: C26H28FeNP This article mentions the following:

Access to highly enantioenriched planar chiral [Cr(5-bromonaphthalene)(CO)₃] (6), [Ru(η⁵-C₅R₅)(5-bromonaphthalene)][PF₆] (42) and [Ru(η⁵-C₅R₅)(4-bromoindene)] (44) was sought using asym. hydrogenolysis of [Cr(5,8-dibromonaphthalene)(CO)₃] (5), [Ru(η⁵-C₅R₅)(5,8-dibromonaphthalene)] (39) and [Ru(η⁵-C₅R₅)(4,7-dibromoindene)] (40), resp. Initial efforts focused on the chromium complex 5. Pd⁰ catalysts with dimethoxyethane as the solvent and LiBH₄ or NaBH₃CN as a hydride source worked best. Nineteen chiral bidentate phosphorus ligands were screened in this reaction. Asym. induction was low to modest with product ee’s in the range of 4 to 52 % and yields of 6 of up to 70 %. Chiral phosphoramidite ligands proved superior and a bulky ligand derived from a Whitesell amine and 3,3′-diphenyl-binaphthol afforded 6 with an ee of 97%. The high enantioselectivity is largely due to the initial desymmetrization reaction though kinetic resolution also plays an important role as shown by the determination of a selectivity factor s = 8.5 at -10°. Initially high ligand loadings (4 equivalent/Pd) were necessary to achieve good asym. induction. This could be traced to the trapping of the chiral ligand by borane formed in the reaction. Addition of 1,4-diazabicyclo[2.2.2]octane (DABCO) suppressed this, and its addition led to the use of Pd and chiral ligand in a 1:1.2 ratio. Asym. hydrogenolysis of cationic dibromonaphthalene and neutral dibromoindenyl complexes of Ru cyclopentadienyl complexes was investigated and afforded the following results: [RuCp(5-bromonaphthalene)][PF₆] (39a; 75%, 90% ee), [RuCp*(5-bromonaphthalene)][PF₆] (39b; 88%, 99% ee), [RuCp(4-bromoindenyl)] (44a; 72%, 96% ee), and [RuCp*(4-bromoindenyl)] (44b; 62%, 68% ee). In the experiment, the researchers used many compounds, for example, (R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2Formula: C26H28FeNP).

(R)-N,N-Dimethyl-1-[(R)-2-(diphenylphosphino)ferrocenyl]ethylamine (cas: 55700-44-2) belongs to chiral phosphine ligands. Phosphine-catalyzed asymmetric reactions are now powerful and versatile tools for the construction of C–C, C–N, C–O, and C–S bonds and for the syntheses of functionalized carbocycles and heterocycles. Trivalent phosphorus compounds called phosphines have a tetrahedral electron-group geometry which makes them structurally analogous to amines.Formula: C26H28FeNP

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis